‫ﺍﻟﻤﺴﺘﻮﻯ ‪ 2 :‬ﺭ ﻭ ﺗﺮ‬

‫ﺍﻣﺘﺤﺎﻥ ﻣﺎﺩﺓ ﺍﻟﻌﻠﻮﻡ ﺍﻟﻔﻴﺰﻳﺎﺋﻴﺔ – ﺍﻟﻔﺼﻞ ﺍﻷﺧﻴﺮ‪............‬ﺍﻟﻤﺪﺓ ‪ 2 :‬ﺳﺎﻋﺔ‬

‫اﻟ‪ /6‬اﻷوﻝ‬
‫‪ -1‬أﻋ ﻲ اﻟ‪E‬ﻎ اﻟ‪E‬ﻒ اﻟﻔ‪E‬ﻠﺔ ﻟﻠ‪D8‬ﺎت اﻟﺎﻟﺔ‪:‬‬
‫‪ -2.3‬ﺜﺎﺌﻲ ﻤ‪$‬ﻞ ﺒ ـ‪ 2‬ـ‪a) 2,3-diméthyl pent-2-éne /‬‬

‫‪s‬‬
‫‪ -3‬إﻴ‪$‬ﻞ ‪ -3.4-‬ﺜﺎﺌﻲ ﻤ‪$‬ﻞ اﻟﻬ*ـ ـ‪1‬ـ‪b) 3-éthyl 3,4-diméthyl hex-1-yne /‬‬

‫‪m‬‬
‫‪c) Propan-2-ol‬‬ ‫ﺒوﺎﻨ(ﻝ ‪2‬‬

‫‪xa‬‬
‫‪d) Ethanol‬‬ ‫اﻴ‪$‬ﺎﻨ(ﻝ‬
‫و اﻟ‪(QR‬ﻝ ‪ .Propan-2-ol‬اﻟ!‪ =8‬ﺒﻘ‪E‬ﺎن‪.‬‬ ‫‪MnO-4‬‬ ‫اﻹرﺠﺎﻋﺔ ﺒ‪ /‬ﺸ(ارد‬
‫اﻹر‬
‫ﻤﻌﺎدﻟﺔ اﻷﻛ=ة اﻹ‬ ‫‪P -2‬‬
‫أﻛ‪ P‬دﻟﺔ‬

‫‪/e‬‬
‫اﻹرﺠﺎﻋﺔ ﺒ‪ /‬ﺸ(ارد ‪ Cr2O72-‬و اﻟ‪(QR‬ﻝ ‪ .éthanol‬اﻟ!‪ =8‬ﺒ‪67‬ﺎدة‪.‬‬
‫اﻹرﺠﺎﻋ‬ ‫‪ -3‬أﻛ‪ P‬ﻤﻌﺎدﻟﺔ‬
‫ﺎدﻟﺔ اﻷﻛ=ة اﻹرﺠ‬

‫‪m‬‬
‫اﻟﻌ‪6(U‬ﺔ ااﻟﺎﺘ‪V‬ﺔ ﻋ‪ /‬اﻷﻛ=ة اﻟﻘ‪=E‬ة ﻓﻲ ‪ 2‬و ‪ 3‬؟ ﺴﻲ اﻟ‪./D8‬‬ ‫‪ -4‬ﻤﺎ ﻫﻲ ‪DT‬ﻌﺔ ‪D8‬ﺎت‬
‫اﻟ‪D8‬ﺎت اﻟﻌ‪U‬‬
‫‪Cr2O72-/Cr3+‬‬ ‫‪...........‬‬ ‫‪MnO-4/Mn2+‬‬
‫‪co‬‬ ‫اﻟ‪$‬ﺎﺌﺎت ‪Ox/Red‬‬
‫ﺎت‬ ‫اﻟﻌ ﺎت ‪:‬‬
‫اﻟ‪ /6‬اﻟ‪$‬ﺎﻨﻲ‬
‫‪n.‬‬
‫ﻋ‪6(U‬ﺔ ‪ CxHyOz‬ﻓﺞ ‪ m1=0.245g‬ﻤ‪ /‬ﻏﺎز ﺜﺎﺌﻲ أﻛ=‬ ‫ﻧﻘﻮﻡ ﺑﺎﻟﺤﺮﻕ ﺍﻟﺘﺎﻡ ﻟـ ‪ 0.1g‬ﻤ‪ /‬ة‬
‫ﻤﺎدة ‪6(U‬ﺔ‬
‫اﻟ‪(R‬ن و ‪ m2=0.100g‬ﻤ‪ /‬اﻟﺎء‪.‬‬
‫‪io‬‬

‫‪. M=72g/m‬‬
‫ﺘﻌ ﻰ اﻟ‪R‬ﻠﺔ اﻟ(ﻟﺔ اﻟ‪[67V‬ﺔ ﻟﻠﺎدة اﻟﻌ‪6(U‬ﺔ ‪M=72g/mol‬‬
‫‪M=72‬‬
‫‪at‬‬

‫اﻷﻛ‪ /V‬ﻓﻲ اﻟ‪.P8‬‬

‫اﻷﻛ‬ ‫‪ -1‬أﺤ‪ P‬اﻟ‪D‬ﺔ اﻟ[(‪6‬ﺔ اﻟ‪R‬ﻠﺔ ﻟ‪R‬ﻞ ﻤ‪ /‬اﻟ‪(R‬ن و اﻟﻬ=روﺠ‪/‬‬
‫ﻬ=روﺠ‪ /‬واﻷ‬
‫‪ -2‬ﺠ= اﻟ‪E‬ﻐﺔ اﻟ‪V‬ﻠﺔ ﻟﻬ^ا اﻟ‪.P8‬‬
‫‪uc‬‬

‫‪ -3‬اﻛ‪ P‬ﻤﻌﺎدﻟﺔ اﻻﺤاق اﻟﺎم ﻟﻬ^ا اﻟ(ع اﻟ‪R‬ﺎﺌﻲ‪.‬‬

‫‪ed‬‬

‫‪ -4‬اﺤ‪ P‬ﺤ‪ V‬ﻏﺎز ﺜﺎﺌﻲ أﻛ= اﻟ‪(R‬ن اﻟﺎﺘﺞ ﻓﻲ ﻫ^ﻩ اﻟﻌﻠﺔ‪.‬‬

‫‪MO=16g/moL‬‬
‫‪=16g/m‬‬ ‫‪MH=1g/mol‬‬ ‫اﻟﻌ ﺎت ‪، Vm=24L/mol :‬‬
‫‪-‬‬

‫‪MC=12g/moL‬‬
‫‪cy‬‬

‫ﻭﺿﻌﻳﺔ ﺇﺩﻣﺎﺟﻳﺔ‬
‫‪ -II‬ﺃﺟﺭﻳﺕ ﻋﻠﻰ ﺛﻼﺛﺔ ﻣﺭﻛﺑﺎﺕ ﻋﺿﻭﻳﺔ ﺍﻟﺗﺟﺎﺭﺏ ﺍﻟﺗﺎﻟﻳﺔ ‪:‬‬
‫‪en‬‬

‫‪CnH2n + H2O‬‬

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 ‫‪ -1‬ﺍﻋﺗﻣﺎﺩﺍ ً ﻋﻠﻰ ﺍﻟﻧﺗﺎﺋﺞ ﺍﻟﺗﺟﺭﻳﺑﻳﺔ ﺍﻟﺳﺎﺑﻘﺔ ﺍﺳﺗﻧﺗﺞ ﻁﺑﻳﻌﺔ ﺍﻟﻣﺭﻛﺑﺎﺕ ‪ B‬ﻭ ‪. C‬‬
‫‪ -2‬ﺇﺫﺍ ﻛﺎﻧﺕ ﺍﻟﻛﺗﻠﺔ ﺍﻟﻣﻭﻟﻳﺔ ﻟﻠﻣﺭﻛﺏ ‪ B‬ﻫﻲ ‪.60 g.mole-1‬‬
‫ﺟﺩ ﺍﻟﺻﻳﻎ ﺍﻟﻌﺎﻣﺔ ﻟـ ‪ B‬ﻭ ‪. C‬‬
‫ﺍﻟﻣﺭﻛﺏ ‪ B‬ﻟﻪ ﺛﻼﺛﺔ ﻣﺗﻣﺎﻛﺑﺎﺕ ﻧﺭﻣﺯ ﻟﻬﺎ ﺑﺎﻟﺭﻣﻭﺯ ‪. F , E , D :‬‬
‫‪ -II‬ﺍﺍﻟﻣﺭﻛ‬

‫‪s‬‬
‫ﺃﻋﻁﻲ ﺻﻳﻐﻬﺎ ﺍﻟﻧﺻﻑ ﺍﻟﻣﻔﺻﻠﺔ‪.‬‬
‫‪ -1‬ﺃﻋ‬

‫‪m‬‬
‫ﺍﻟﻣﻣﺎﻛﺑﺎﺕ ‪ B , E , D :‬ﺑﻣﺣﻠﻭﻝ ‪ KMnO4‬ﻓﻲ ﻭﺳﻁ ﺣﻣﺿﻲ ﻓﻧﺣﺻﻝ ‪:‬‬
‫ﺍﻟﻣﻣﺎﻛﺑﺎ‬
‫‪ -2‬ﻧﻌﺎﻟﺞ ﺍﻟﻣﻣ‬

‫‪xa‬‬
‫‪E‬‬ ‫‪D‬‬ ‫‪B‬‬ ‫ﺭﻛﺏ‬
‫ﺍﻟﻣﺭﻛﺏ‬

‫‪/e‬‬
‫‪E1‬‬ ‫ﻻﺷﻲء‬ ‫‪B1‬‬ ‫ﺍﻟﻧﺎﺗﺞ‬
‫ﺞ‬

‫‪om‬‬
‫ﺃﻛﺳﺩﺓ ﻣﻘﺗﺻﺩﺓ؟ ﻣﺎﺫﺍ ﺗﺳﺗﻧﺗﺞ؟‬
‫‪ -1-2‬ﺃﻱ ﻣﻣﺎ ﻛﺏ ﻟﻟﻡ ﺗﺣﺩﺙ ﻟﻪ ﺃﻛﺳﺩ‬
‫ﺑﻳﻥ ‪ B‬ﻭ ‪E‬؟ ﺛﻡ ﺑﻳﻥ ‪ B‬ﻭ‪ D‬؟‬
‫ﺍﻟﺗﻣﺎﻛﺏ ﻥ‬
‫ﺏ‬ ‫‪ -2-2‬ﻣﺎ ﻧﻭﻉ‬
‫‪.c‬‬
‫‪ DNPH‬ﻭ ﻣﺣﻠﻭﻝ ﻛﺎﺷﻑ ﺷﻳﻑ ﻓﻛﺎﻧﺕ ﺍﻟﻧﺗﺎﺋﺞ ﺍﻟﺗﺎﻟﻳﺔ‪:‬‬
‫ﻟﻛﺎﺷﻑ ‪NP‬‬
‫‪ -3‬ﻧﺧﺿﻊ ﺍﻟﻣﺭﻛﺑﻳﻥ ‪ E1 , B1‬ﺷﻑ‬
‫‪n‬‬
‫‪tio‬‬

‫ﻛﺎﺷﻑ ﺷﻳﻑ‬ ‫‪DNPH‬‬ ‫ﺍﻟﻣﺭﻛﺏ‬

‫‪-‬‬ ‫‪+‬‬ ‫‪B1‬‬
‫‪ca‬‬

‫‪+‬‬ ‫‪+‬‬ ‫‪E1‬‬

‫‪du‬‬

‫ﺗﻣﻳﺯﻫﺎ؟‬
‫ﺗﻣﻳﺯﻫ‬
‫ﻅﻳﻔﻳﺔ ﺍﻟﺗﻲ ﺗﻣﻳ‬
‫‪ -a‬ﻣﺎ ﻫﻲ ﺍﻟﻭﻅﻳﻔﺔ ﺍﻟﺗﻲ ﺗﻡ ﺍﻟﻛﺷﻑ ﻋﻧﻬﺎ ﺗﺟﺭﻳﺑﺎ؟ ﻭﻣﺎ ﻫﻲ ﺍﻟﺯﻣﺭﺓ ﺍﻟﻭﻅﻳﻔﻳﺔ‬
‫‪ -b‬ﻣﺎ ﻫﻲ ﺍﻟﺻﻳﻐﺔ ﺍﻟﻣﻔﺻﻠﺔ ﻟـ ‪ E1‬ﻭ ‪B1‬؟ ﻭﻣﺎ ﺍﺳﻣﻬﻣﺎ؟‬
‫‪-e‬‬
‫‪cy‬‬
‫‪en‬‬

‫ﺑﺎﻟﺘﻮﻓﻴﻖ‬

‫ﺍﻷﺳﺘﺎﺫ ‪ :‬ﻣﺴﺆﻭﻝ ﺍﻟﻤﺎﺩﺓ‬

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 ‫ﻣﺎدة ‪ :‬ﻓﻴﺰﻳﺎء ‪ +‬ﻛﻴﻤﻴﺎء‬ ‫اﻟﻤﺪة ‪ 2 :‬ﺳﺎﻋﺔ‬ ‫اﻟﻤﺴﺘﻮى ‪ 2 :‬ع ت ‪ 2‬ر و ‪ 2‬ت ر‬

‫ﺗﺼﺤﻴﺢ اﻣﺘﺤﺎن اﻟﻔﺼﻞ اﻟﺜﺎﻟﺚ‬

‫ﺍﻟﺗﻣﺭﻳﻥ ﺍﻷﻭﻝ ‪ 7.5:‬ﻧﻘﻁﺔ ‪ -1‬ﺍﻟﺻﻳﻎ ﺍﻟﻧﺻﻑ ﺍﻟﻣﻔﺻﻠﺔ‪.‬‬

‫ﺍﻟﺗﻣ‬
‫‪01 x 4‬‬ ‫‪H3C‬‬

‫‪s‬‬
‫‪CH2‬‬ ‫‪CH3‬‬
‫‪OH‬‬

‫‪m‬‬
‫‪HC‬‬ ‫‪C‬‬ ‫‪C HC‬‬ ‫‪H3C‬‬ ‫‪CH3‬‬
‫‪H3C HC‬‬ ‫‪1‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪4‬‬
‫‪1‬‬ ‫‪2‬‬
‫‪CH3‬‬ ‫‪CH3‬‬ ‫‪CH2 CH3‬‬ ‫‪H3C‬‬ ‫‪C‬‬ ‫‪C‬‬ ‫‪CH2‬‬ ‫‪CH3‬‬ ‫‪H3C‬‬ ‫‪CH2‬‬ ‫‪OH‬‬
‫‪O‬‬‫‪H‬‬
‫‪6‬‬ ‫‪2‬‬ ‫‪3‬‬ ‫‪5‬‬ ‫‪2‬‬

‫‪xa‬‬
‫‪3‬‬ ‫‪5‬‬ ‫‪1‬‬ ‫‪4‬‬ ‫‪1‬‬

‫ﺍﻻﺭﺟﺎﻋ‬
‫ﻣﻌﺎﺩﻟﺔ ﺍﻷﻛﺳﺩﺓ ﺍﻻﺭﺟ‬
‫ﺍﻻﺭﺟﺎﻋﻳﺔ‪:‬‬ ‫‪ -2‬ﺩﻟﺔ‬

‫‪/e‬‬
‫‪0.5 x 3‬‬
‫‪2(MnO4- + 8H+ + 5 é = M‬‬ ‫)‪2 + 4 H O‬‬
‫‪Mn2+‬‬ ‫‪2‬‬

‫‪5(CH3CHOH-CH3 = CH3-CO‬‬ ‫)‪C 3 + 2H+ + 2é‬‬

‫‪C -CH‬‬

‫‪m‬‬
‫‪2MnO4- + 6H++5 CH3CH(OH)-CH3 =5CH3-CO‬‬ ‫‪C 3 +2 Mn2++ 8 H2O‬‬
‫‪C -CH‬‬
‫‪co‬‬ ‫ﻣﻌﺎﺩﻟﺔ ﺍﻷﻛﺳﺩﺓ ﺍﻻﺭﺟﺎﻋﻳﺔ‪:‬‬
‫)‪2(Cr2O72- + 14H+ + 6 é = Cr3+ + 7 H2O‬‬
‫‪n.‬‬
‫‪0.5 x 3‬‬
‫‪3(CH3-CH2OH+‬‬
‫‪O‬‬ ‫)‪H2O = CH3-COOH + 4H+ + 4é‬‬
‫‪tio‬‬

‫‪2Cr2O72- + 16H‬‬
‫‪6H+ + 3CH3-C‬‬
‫‪CH2OH+ =2 Cr3+ +11H2O +3 CH3-COOH‬‬
‫‪ca‬‬

‫‪ -4‬ﻓﻲ ﺍﻟﺣﺎﻟﺔ ‪ 2‬ﺍﻟﻣﺭﻛﺏ ﺍﻟﻌﺿﻭﻱ ﻛﻳﺗﻭﻥ ‪propanone‬‬

‫‪pr‬‬
‫‪0.25 x 2‬‬
‫ﻓﻲ ﺍﻟﺣﺎﻟﺔ ‪ 3‬ﺍﻟﻣﺭﻛﺏ ﻫﻭ ﺣﻣﺽ ﻛﺭﺑﻭﻛﺳﻳﻠﻲ ‪éthanoïque‬‬
‫‪du‬‬

‫ﺍﻟﺗﻣﺭﻳﻥ ﺍﻟﺛﺎﻧﻲ ‪ 5.5‬ﻧﻘﻁﺔ‬

‫‪1x3‬‬ ‫‪Pc = 67%‬‬ ‫‪PO = 22%‬‬ ‫‪ -1‬ﺍﻟﻧﺳﺏ ﺍﻟﻣﺋﻭﻳﺔ ﺍﻟﻛﺗﻠﻳﺔ ‪PH = 11% :‬‬
‫‪-e‬‬

‫‪0.5‬‬ ‫‪ -2‬ﺍﻟﺻﻳﻐﺔ ﺍﻟﻣﺟﻣﻠﺔ ‪. C4H8O‬‬

‫‪cy‬‬

‫‪ -3‬ﻣﻌﺎﺩﻟﺔ ﺍﻻﺣﺗﺭﺍﻕ ‪:‬‬

‫‪01‬‬
‫‪C4H8O+ 11/2O2 = 4CO2 + 4H2O‬‬
‫‪en‬‬

‫‪-4‬‬ ‫‬
‫‪0.5‬‬
‫‪0.5‬‬

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 ‫ﺍﻟﺗﻣﺭﻳﻥ ﺍﻟﺛﺎﻟﺙ ‪ 07 :‬ﻧﻘﻁﺔ‬
‫‪0.25x2‬‬
‫‪ -1‬ﺍﻟﻣﺭﻛﺏ ‪ B‬ﻛﺣﻭﻝ ‪ ،‬ﺍﻟﻣﺭﻛﺏ ‪ C‬ﻛﻳﺗﻭﻥ‪.‬‬
‫‪0.5‬‬ ‫‪ -2‬ﺍﻟﺻﻳﻐﺔ ﺍﻟﻌﺎﻣﺔ ‪ CnH2n+2O‬ﻭﻣﻧﻪ ‪ M=14n+18=74‬ﻭﻣﻧﻪ ‪.n=3‬‬

‫‪0.5x2‬‬ ‫ﺍﻟﻣﺭﻛﺏ ‪ ، C3H8O - B‬ﺍﻟﻣﺭﻛﺏ ‪.C3H6O - C‬‬

‫ﺍﻟﻣ‬

‫‪s‬‬
‫‪-1 -II‬‬

‫‪m‬‬
‫‪CH2‬‬ ‫‪CH2 OH‬‬ ‫‪OH‬‬
‫‪O‬‬ ‫‪H‬‬
‫‪0.5x3‬‬ ‫‪H3C‬‬ ‫‪CH3‬‬ ‫‪H3C‬‬ ‫‪CH2‬‬ ‫‪H3C HC‬‬ ‫‪CH3‬‬

‫‪xa‬‬
‫‪O‬‬

‫ﺍﻟﻣﻣﺎﻛﺏ ‪ D‬ﻟﻡ ﺗﺣﺩﺙ ﻟﻟﻪ ﺃﻛﺳﺩﺓ ﻣﻘﺗﺻﺩﺓ ﻭﻣﻧﻪ ﺍﻟﻣﻣﺎﻛﺏ ‪ D‬ﻫﻭ ﺍﻟﻣﺭﻛﺏ ﺫﻱ ﺍﻟﺻﻳﻐﺔ ﺍﻟﻧﺻﻑ ﺍﻟﻣﻔﺻﻠﺔ‬
‫ﻣﻣﺎﻛﺏ‬
‫ﻛ‬ ‫‪-1-2‬‬
‫‪CH2‬‬

‫‪/e‬‬
‫‪0.5‬‬
‫‪H3C‬‬ ‫‪CH3‬‬
‫‪O‬‬

‫‪om‬‬
‫‪0.5x2‬‬ ‫ﻭﻅﻳﻔﻲ‪ ،‬ﺃﺃﻣﺎ ‪ B‬ﻭ ‪ E‬ﻣﻭﺿﻌﻲ‪.‬‬
‫‪ -2-2‬ﻧﻭﻉ ﺍﻟﺗﻣﺎﻛﺏ ﺑﻳﻥ ‪ D‬ﻭ ‪ E‬ﻭﻅ‬
‫‪O‬‬
‫‪C‬‬
‫ﺯﻣﺭﺓ‬ ‫‪ DNPH‬ﻫﻲ ﺍﻷﻟﺩﻫﻳﺩﻳﺔ ﺃﻭ ﺍﻟﻛﻳﺗﻭﻧﻳﺔ ﻭﺍﻟﺯﻣﺭﺓ ﻫﻲ‬
‫‪ -a -3‬ﺍﻟﻭﻅﻳﻔﺔ ﺍﻟﺗﻲ ﺗﻡ ﺍﻟﻛﺷﻑ ﻋﻧﻬﺎ ﺑــ ‪NP‬‬
‫‪.c‬‬
‫‪O‬‬
‫‪0.5x2‬‬ ‫‪C‬‬
‫‪n‬‬
‫‪.‬‬ ‫‪H‬‬ ‫ﻭﺍﻟﺯﻣﺭﺓ ﺍﻷﻟﺩﻫﻳﺩﻳﺔ‬
‫ﺍﻷﻟﺩﻫﻳﺩﺍﺕ ﻭﺍﻟﺯ‬
‫ﺍﻟﻛﺭﺑﻭﻧﻳﻝ‪ ،‬ﺃﻣﺎ ﻛﺎﺷﻑ ﺷﻳﻑ ﻓﻳﻛﺷﻑ ﻋﻥ ﺩﻫﻳﺩﺍﺕ‬
‫‪tio‬‬

‫‪O‬‬
‫‪0.25x2‬‬ ‫‪E1 H3C‬‬ ‫‪C‬‬ ‫‪CH3‬‬
‫‪propanone -b -3‬‬
‫‪ca‬‬

‫‪O‬‬
‫‪CH2‬‬
‫‪C‬‬
‫‪0.25x2‬‬ ‫‪H3C‬‬
‫‪B1‬‬ ‫‪H‬‬ ‫‪prpanal‬‬
‫‪du‬‬
‫‪-e‬‬
‫‪cy‬‬
‫‪en‬‬

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